My Week in Points: how much work is too much work?

The Point Me to the Plane Meet-Up on Thursday in NYC was great fun, especially for me as I got billing on the event just for showing up. Thanks Adam for putting together a great time! Not having to put in an effort while seeing the creative Vanilla Reload necklace on the Frugal Travel Lawyer that spoke of countless time many of us have spent in their pursuit put me in a reflective mood on this hobby. Chatting with the attendees, each with things to teach me and tales of their exploits, I was interested to see the people who talk of the burning and people who talk of the earning.

There are many for whom the earning is the thrill and the big payoff, and they are engaged in a arm’s war of ever-more elaborate and creatives schemes that leave me in awe. I try to skim off what I can manage. The back and forth this week at Million Mile Secrets and FrequentMiler on gift cards with PIN is the latest example, and if I had a convenient Walmart it might work for me to partake.

It’s also tax time in the US and I studied Frequent Miler’s masterful Pay federal taxes by credit card, almost for free. I have a small amount to pay on federal taxes, not worth any particular effort, though it left me wondering at what amount I would deem it worthwhile to go the full Big Crumbs-Amex gift card route. The intoxicating lure of miles would probably get me to do it for far less than a cost-benefit analysis would suggest.

I seldom cover miles and points on this blog, many others know much more and have much more time to cover these subjects. There may be an opening to speak to people who want to spend less time on this hobby. I would like to spend much less without giving up the best benefits. I have a few ideas that I will try out on the blog. If I dare to write about a deal that many others have covered I will open myself up to the repetition criticism. Hopefully I will offer something different and useful to those trying to keep a little balance in their life.

I did little this week other than rant about Delta’s slaughter of the same-day confirmed program, so here are 3 posts that were particularly useful to me:

I continue my search for a good use of Virgin Atlantic points. There are many partners but each partner has quirky rules. One Mile at a Time suggests that Virgin America is worth keeping in mind. My wife has been asking for a trip to San Francisco and 25,000 roundtrip in economy with apparently good availability seems pretty decent (keep in mind I coming from a Delta award perspective!).

I am not in a position to take advantage of this but FrequentMiler expanded on a One Mile at a Time piece suggestion of an interesting play for moving Ultimate Rewards or Marriott Rewards Points to US Airways with a 50% boost until April 30. The most attractive option for some is the Marriott Flight and Hotel package. I suppose if I had kids a 7-night hotel stay might be appealing to me. Deals We Like breaks down the exchange rates for several other options.

I thought you were going to American Samoa on virgin? I would love to hear about such a trip as I am a bit on the fence about going. There does not appear to be much there…. or maybe I just dont know.

I am with you on the time thing. I agree that some people are going overboard. I would like to spend less time on this hobby and probably could. Like you said the promise of seeing new countries keeps me at it. And often when I am buying something for $20 online and going through a portal, I wonder… what am I doing… If it works I am going to get 100 miles for this….

@john – My Virgin America points from their credit card should cover the American Samoa trip. I separately have the Virgin Atlantic points from that credit card, fortunately never took the bait on 1:2 to Hilton. But now I have a new plan for Memorial Day, pending ability to get coveted transit visa a la uprgd Matthew. I have not researched American Samoa much, I have been a few Micronesian islands and the Solomons, my enjoyment is directly proportional to how much of WWII is still left to see.

Paying taxes for points is my holy grail. As someone who has zero withholding, I’m responsible for all my local, state, and federal tax payments. Because of the penalties associated with underpayment for the self-employed, I make sure that I overpay enough to get a significant refund each year.
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In a low-interest, high-points environment I would be happy to play it even safer and have a higher margin of over-payment if I knew that allowing the government to use my money for a month or two was accompanied by a free ticket to Europe.
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That said, I’ve never jumped on the Bluebird / Vanilla debit card thing since it seems like an enormous amount of work (constantly ferreting out the $500 cards) but even more — that it might produce in the card issue the impression that I was doing something not entirely licit.

@john – As far as I know, too, there is nothing WWII there so I expect I would just do a quick touchdown. My favorite so far is the Solomon Islands, I need to get those posts up. Also, Peliliu off Palau, in college I read With the Old Breed and it was awesome to see the island in person.